The Problem With Devil’s Advocates

Sometimes I write something and it seems like total bullshit. Other times, I think it is good, then realize weeks or months later that it was total bullshit. For example, a while back I suggested that leaders not surround themselves with suckups. I've consistently preached that you should hire people who are different from you, and in many cases assign someone to play devil's advocate when discussing a new idea. But there is a problem. People who disagree with you are sometimes difficult to get on board when you make a decision that they don't agree with. They don't give it their all, probably because deep down they hope to help it fail.

This is a strategy vs. execution problem. If you have a team of "yes-men" around you, no one will question your decisions. You may miss important problems with your idea, and thus develop a poor strategy. However, since everyone agrees with you, the execution of that bad strategy is good.

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Alternatively, if you surround yourself with people who disagree with you and look at the world very differently, they will point out problems with your ideas and thus you can develop a better strategy. But, some of them may not be on board when it comes time to execute, and that can be a problem.

This is where leadership comes in. A good leader has to encourage people to shoot holes in his/her ideas, but then turn around and obtain buy-in from those same people. The only way to execute effectively is if everyone is on board – even the people who disagree with the strategy. Leaders have to be passionate, convincing, and persuasive for this very reason. It is the only way out of the dilemma.